William H. Macy

15. CAKE (2014)

14. MR. HOLLAND’S OPUS (1995)

13. AIR FORCE ONE (1997)

12. WAG THE DOG (1997)

11. A CIVIL ACTION (1998)

10. PLEASANTVILLE (1998)

9. ROOM (2015)

8. HAPPY TEXAS (1999)

7. HOMICIDE (1991)

6. THE COOLER (2003)

5. OLEANNA (1994)

4. MAGNOLIA (1999)

3. BOOGIE NIGHTS (1997)

2. SEABISCUIT (2003)

1. FARGO (1996)

William H. Macy received his fifth Emmy nomination in 2018 for playing Frank Gallagher, the outright horrible father of the Gallagher clan on “Shameless.” In total Macy has received a whopping 14 Emmy nominations for his work as an actor, writer, and producer. He won for two of those nominations back in 2003 for his acting and writing the TV movie “Door to Door.” While he has yet to take home an Emmy for “Shameless,” he has won the Screen Actors Guild Award three times. But it’s his film career for the focus of our photo gallery above, so take a tour of Macy’s 15 greatest movies, ranked from worst to best.

Macy had a long career on the stage and in episodic television and film, seemingly destined to be one of those actors who works steadily but never really becomes a household name. That changed in the mid-1990s. After appearing in roughly 15 plays off-Broadway often by his mentor and former college professor David Mamet, Macy landed a recurring role on the highly popular “ER.” That visibility led to him being cast in the Coen brothers film “Fargo” which earned him an Oscar nomination for Best Supporting Actor. His movie career has also included such greats as “Seabiscuit,” “The Cooler,” “Magnolia” and “Boogie Nights.”

Macy had a supporting role alongside his real-life wife Felicity Huffman in this Jennifer Aniston film. Unlike a lot of Aniston’s comedic films this was a dark drama about a woman dealing with the death of her son in a car accident. Aniston had a good run with pre-Oscar awards but ultimately was left out of the Best Actress Oscar race.

“Mr. Holland’s Opus” was a surprise hit in 1995 and returned Richard Dreyfuss to the Oscar race after an almost 20-year absence (he had won the Best Actor award for “The Goodbye Girl” in 1977 and earned another Best Actor nomination here.) Dreyfuss played Mr. Holland, a dedicated high school music teacher who fights to keep music in the schools at a time when arts were being cut from the curriculum. Macy plays the Vice Principal of the school who is one of Mr. Holland’s detractors.

Harrison Ford plays the president of the United States in this action film about the battle between the US and Russia. In this case the president literally has to physically battle the Russians when a terrorist group led by Gary Oldman takes over the President’s plane. Macy plays part of the president’s military staff who is also onboard the hijacked aircraft.

“Wag the Dog” was a satirical political comedy lampooning some of the events of the Bill Clinton presidential administration and the scandal after his affair with White House intern Monica Lewinsky. The title phrase refers to when a president launches some sort of military action in order to distract from some personal crisis. Macy plays one of the CIA agents who is involved in the political maneuvering.

Director and writer: Steven Zaillian. Starring John Travolta, Robert Duvall, John Lithgow.

Macy was among the all-star ensemble of this film about lawyers crusading against and trying to get justice for people who have been hurt by contaminated drinking water. Two years later the similarly themed “Erin Brockovich” would chart similar territory to more box office and Oscar success. This film is mostly notable for Robert Duvall’s Oscar nominated Best Supporting Actor performance.

Macy won the Boston Society of Film Critic’s Award for Best Supporting Actor for this fantasy about an introverted modern-day teenager who loves watching an innocent 1950s sitcom on television then magically finds he and his sister have been transported thru their TV and now live in the sitcom. The film is reminiscent of movies like “The Truman Show” and “The Purple Rose of Cairo” that blur the difference between reality and the media. This is a topic that has only become more topical in the years since these films were released.

Brie Larson won a Best Actress Oscar for this film which tells the story of a teenager who is kept hostage in a small room where she is raped and conceives a child and subsequently raises him all in one small room. Macy plays her father whom she is reunited with once she and her son escape from their prison. Macy is very moving when he is finally reunited with the daughter he feared dead and also has a tender moment with his grandson when he tries to gain the kid’s trust through the boy’s interest but standoffishness with a family dog.

Macy won a Satellite Award for Best Supporting Actor in a Comedy for this story of three escaped convicts who pose as gay beauty pageant coordinators. Macy who plays the Sheriff of the small town the men are hiding out and develops a romantic interest in one of the convicts not knowing that he is not really gay and is in fact on the run from the law.

Macy was nominated as Best Supporting Actor by the Independent Spirit Awards for his role in a film written and directed by his mentor David Mamet. Macy plays a homicide detective and partner of the lead character played by Joe Mantegna. The film deals with the main character’s investigation of a death and also his own relationship to his Jewish heritage.

In this Las Vegas casino set drama Macy plays a man who is so bad at gambling that the casino actually pays him to sit next to successful gamblers in the hopes that some of his bad luck will rub off on them. Macy plays the sad sack character to perfection but it was Alec Baldwin in a supporting role who walked away with an Oscar nomination for the film.

Director and writer: David Mamet. Starring Debra Eisenstadt.

Macy created this role in the original off-Broadway production of David Mamet’s highly controversial play. He recreated the role on film under Mamet’s direction. Written in response to the controversy of the Anita Hill/Clarence Thomas Supreme Court hearings Oleanna tells the story of a college professor and one of his students. The woman starts making sexual harassment allegations against the professor after being encouraged to do show by a female activist group on campus. Her accusations become increasingly demanding and she seems to be trying to blackmail the professor into helping her censor certain books from the college’s curriculum. The movie had a quieter response than the play but the play was a hot button theater piece which reportedly had people yelling out to the actors since they were becoming so enraged by the sensitive subject matter.

“Magnolia” brought together a large ensemble cast for Paul Thomas Anderson’s take on life in the San Fernando Valley of Los Angeles. While the film’s ending didn’t sit well with many it didn’t manage to receive a few Oscar nominations including one for its screenplay and one for Tom Cruise as Supporting Actor. Macy plays a former television whiz kid who has fallen on hard times since his parents spent all his childhood winnings and he had become mentally impaired after being struck by lightning.

Macy plays a doomed man in the porn star industry for writer/director Paul Thomas Anderson examination of the 1970’s porn industry. The film was nominated for three Oscars. Anderson received a Best Original Screenplay nomination while Julianne Moore and Burt Reynolds each received supporting acting nominations. Reynolds had a love/hate relationship with the film. While it finally got him the Oscar nomination he had been denied for other acclaimed performances like “Deliverance” and “Starting Over” Reynolds feared the film was too sexually explicit and would alienate his core fan base. Macy himself has said when he first got the script he feared the film would be X-Rated and unreleasable to a mainstream audience.

This story of how a race horse named Seabiscuit lifted the spirits of America during the great depression received seven Oscar nominations including Best Picture. Macy has a great role as one of the sports announcers who calls Seabiscuit’s races. He is quite excellent in the role and expertly captures the old-time radio sound announcers of that era used. He was nominated for a Golden Globe as Best Supporting Actor for the film.

Macy had been a working actor for many years on stage, screen and television but it wasn’t until his role as Jerry Lundegaard, a car salesman in need of cash who launches a fool hearted plan to kidnap his own wife to extort money from her rich father. The plan ends tragically for all involved. The mystery is solved by Frances McDormand in her first Best Actress winning performances. Macy also received his share of award recognition chief among them a Best Supporting Actor Oscar nomination.